Azo-dyestuff and fiber dyed therewith



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Patented June .11, 1935 I 2,004,383 H AZO-DYESTUFF AND FIBER DYEI):

THEREWI TH Kurt Schimmelschmidt; and. Q

Frankforhon-the-Mainf General Aniline Works, a corporation of Delaware A plicationkugust 9.1 1934." serial Y j G? ytasslgmu's 1 min.

No. 738,882. In Germanyphugmtsl}, 1333 Lef present. invention relates" 7 following formula obtainable by combining, in substance, on the fiber or on a substratum which is adaptedfor the production of lakes, the diam-compound of 5- chloro-l-aminobenzene-2-sulfonic acid dimthylamide, with 2,3-hydroxynaphthoic acid anilide. When the dyestuif is produced in the usual manner on the fiber, a golden-orange shade of a very good fastness to light is obtained. f

This result is surprising, as, for instance, the

dyestuff prepared from 2,3-hydroxy-naphthoic acid anilide and the diazo-compoundof 2--chlorol l fifi q i' st'ufi and to fiberdyed therewith; more. partieu; larly itrelatesl. to. a. dyestufl corresponding; to the -aminobenzene-5sulfonic acid dimethylamide, a compoundwhich contains the sulfonic acid dithen to the pants 1 being by .weight,- ,unl ess otherwise stated: g

(l) .50 grams of boiled in 1 liter of the s d r-m developed, insthe moisttstate, in the dye bathr cotton yarn are. treated groundingliquor. for half, an hour,

. The dyed yarn is rinsedfsoaped at boiling temperature and dried.

methylamide radical in m-position to the aminogroup (German Patent 480,814) yields on the fiber scarlet-red dyeings the fastness .to light of which is inferior to that of the dyestufi prepared 3 from the diazo-compound of 5-chloro-1-aminobenzene-Z-sulfonic v acid dimethylamide; The displacement of theshade to the yellow side of the spectrum and the increase of the fastness' to light by exchangingthe substituents of the diazo-component, could in no way be foreseen.

The azo-dyestuff obtainable according to the present process may also very wellbe produced on the fiber in the printing processby using the diazo-compound in theform of the stable zincchloride double-salt and printing it on the material grounded with the coupling component.

Without a long after-treatment bysoaping at boiling temperature there is immediately obtained the desired golden-orangetint' which could not be obtained, hitherto, with the 2,3-hyd'roxynaphthoic acid anilide used almost exclusively in print v ing processes and with the commercial diazo-components. The azo-dyestufi, obtainable according to the present process, represents, therefore, a

. valuable technical enrichment;

The following examples serve to illustrate the invention, but they are not intended to limit it ((1) Grounding liquor are-dissolved in 1 12 cc. of alcohoL- H 3 cc. of caustic soda solution of 34 B.,

3 cc. of formaldehyde solution of 30 per cent. 1 strength and 1 6 grams of 2,3-hydroxynaphthoic acid anilide 1 V 6 cc. of water and madeu p with 10 cc. of Turkey redoil of per cent. strength, 7 cc. of caustic'soda solution of 34B. and

V water to 2 1 liter.

g (b) Dye bath 2.3 grams of 5-chloro-1-aminobenzene-2-sulfonic acid dimethylamide are dissolved in 2 10 cc. of acetone; a e 3.1 cc. of hydrochloric acid of 20 B. are

i added and, after. addition of 10 grams of ice, the whole is diazotized with 8 cc. of a solution of sodium nitrite 1:10. 3

The diazo-solution is neutralized with sodium.

acetate and, after addition of common salt and water, made up tO'l liter. 7 i A vivid golden-orange shade of good fastness properties, especially of a very good fastness to, 'light and to ironing, is obtained.

(2) A" solution of the diam-compound prepared in the usual manner from 23.5 parts of 5- chloro-1-aminobenzene-2-sulfonic acid dimeth ylamideis allowed to run into an aqueous suspension of 26.3 parts of 2,3-hydroxynaphth0ic acid anilide prepared by dissolving the anilide in .an alcoholic caustic sodasolution, diluting with water and neutralizing with acetic acid.

After. termination of the coupling reactiomthe dyestufi is filtered by suction, washed until neutral and dried; it forms an orangeecolored powder. v v l (3) Printing prescription 1 The materialto be printed is grounded on the foulard, printed, dried, passed through a hot sodiumcarbonate bath (2 grams per liter), rinsed, soaped at boiling temperature and rinsed again. 7

water by wringing; or. eentrifugjng and t (a) Grounding liquor 15 grams of 2,3-hydroxynaphthoic acid anilide are dissolved in 20 cc. of Turkey red oil and 18 cc. of caustic soda solution of 38 B. and

made up with water to 1 liter.

(2)) Printing color 6.5 grams of a dyeing salt containing. the? zinc-chloride double-salt of the diazonium-chloride from 5-chloro-1-aminobenzene-Z-sulfon'ic acid dimethy1am-' i. ide, diluted with anhydrous sodium sulfate (:13 grams of the base) are dissolved in of acetic acid of and 48.5 cc. of water.

' 5 cc. per cent. strength 40 cc. of wheat starch-tragacanth-thickening are then added.

grams of printing color.

A vivid golden-orange tint of very good fastness properties is obtained as in Example 1.

By using for the preparation of the printing color, instead of acetic acid, 10 cc. of an aqueous solution of, aluminium-sulfate (1:1), the printing color may be used as resist under dyeings with diam-compounds from aminodiphenylaminc-derivatives.

We claim: 1. The azo-dyestuff of the following formula:

' yie1ding,,when produced on the fiber, a vivid golden-orange shade of good fastness properties, particularly of very good fastness to ironing and to light.

' 2. Fiber dyed with the azo-dyestuff 'as claimed in claim 1.

KURT SCHIMMELSCHMIDT. HANS THOMAE. 

